Method for increasing sugar content of sugar cane



United States Patent Ofiice 3,224,865 Patented Dec. 21, 1965 3,224,865 METHOD FDR INCREASING SUGAR CONTENT OF SUGAR CANE Arne E. Carlson, Wilmington, Del., assignor to E. I. du

Pont de Nemours and Company, Wilmington, Del., a

corporation of Delaware No Drawing. Filed Nov. 20, 1962, Ser. No. 239,074

3 Claims. (Cl. 71-2.6)

This invention relates to the hormonal treatment of sugar cane and is more particularly directed to the application of the benzoic acid compounds disclosed in French Patent 1,224,787, delivre February 8, 1960, to sugar cane for increasing its maximum sugar yield.

The invention in its preferred form uses mixtures of at least one such benzoic acid compound in admixture with one or more surface-active agents which can be those known as wetting agents, detergents, or emulsifying agents.

According to the present invention hormonal effects which are manifest by an increase in the sugar content of sugar cane are produced by the application of proper amounts of these benzoic acid compounds with or without surfactants at an appropriate time prior to harvest. In addition, application of the benzoic acid compounds assures that maximum sugar content will be obtained despite possible unfavorable weather conditions occurring during the ripening period.

The benzoic acid compounds used in compositions of the invention should be sterically hindered. These are compounds in which both of the positions ortho to COOH are substituted and are represented as follows:

COOH

The compounds as thus shown can include: 2,3-dichloro-6-rnethylbenzoic acid, 2'rnethyl-3,6-dichlorobenzoic acid, etc.

It is preferred for purposes of the present invention to use com ositions which contain one or both of 2,3-dichloro-6-methylbenzoic acid and 2-methyl-3,6-dichlorobenzoic acid.

Grdinarily the benzoic acid compounds will be a mixture of the preferred sterically hindered isomers together with other isomers which are less active but which still contribute. Formulations can be prepared as described in the above-mentioned French patent to obtain a mixture of methyldichlorobenzoic acids as follows:

Percent 2,3-dichloro-6-methylbenzoic acid 85 2-methyl-3,6-dichlorobenzoic acid 15 By using the precursor compound prepared as in EX- ample 1 a mixture is obtained which contains 10 or different compounds. The principal components are the four components shown at the end of Example 1 of the above-mentioned French Patent and are present as major components.

The benzoic acid compounds can be used as the acid and as such salts as the sodium, potassium, ammonium, monomethylamine, dimethylamine, trimethylamine, ethanolamine, diethanolamine and triethanolamine salts. The

sodium salt and triethanolamine salt offer particular advantages and are preferred.

Hormonal compositions of the invention can be made ready for use by pelleting before application or by dissolving in a solvent or suspending in an oil. Preferably in all such compositions a surfactant will be included. The surfactant can be a wetting agent, a detergent or an emulsifying agent.

The surfactants or surface-active agents can include such anionic, cationic, and nonionic surface-active agents as have heretofore been generally employed in pest control compositions. Suitable surface-active agents are set out for example in Searle U.S. Patent No. 2,426,417; Todd, US. Patent No. 2,655,447; Jones, US Patent No. 2,412,- 510; or Lenher US. Patent No. 2,139,276.. A detailed list of such agents is set forth in Detergents and EmulsifiersUp to Date, 1962, by John W. McCutcheon, Inc., and Bulletin E-607 of the Bureau of Entomology and Plant Quarantine of the US. Department of Agriculture.

In general, a preferred group of surfactants are those which have a strong tendency to lower the surface tension of water at a water-air interface. Thus, the surface tension of water is reduced from 72 dines per centimeter to something under 54, even more preferable, to something under 40 by the inclusion of 0.01% by weight of the surfactant in water. Typically some of the preferred commercial surfactants at the rate of 0.01% by weight in water will reduce surface tension to about 35 dines per centimeter. It is noted however, that the correlation between effectiveness in reducing surface tension and effectiveness for purposes of the invention is an empirical observation and it is doubted that lowering of surface tension per se is the principal function of these agents in compositions of the invention. This follows because surface tension is not greatly reduced by the addition of large quantities of surfactant and yet according to the invention large quantities produce the results herein achieved and the results are therefore inferably not merely the result of lowering surface tension. Some agents of higher surface tension can probably be used with some of the benefits of the invention without realizing them to the fullest extent.

Suitable surfactants for use in compositions of the present invention are alkyl and alkyl aryl polyether alcohols, polyoxyethylene sorbitol and sorbitan acid esters co-reacted with ureas, polyethylene glycol fatty esters and fatty alkylol amide condensates, alkyl aryl sulfonates, fatty alcohol sulfates, dialkyl esters of sodium sulfosuccinate, fatty acid esters of sodium isethionate, polyoxyethylene thioether, and long-chain quaternary ammonium chloride.

Among the more preferred surfactants are those anionic and nonionic agent-s recognized as wetting agents, detergents, or emulsifiers. Among anionic surfactants preferred ones are alkali metal, or amine salts of alkyl benzene sulfonic acids such as dodecylbenzene sulfonic acid, sodium lauryl sulfate, alkyl naphthalene sulfonates, sodium N-methyl-N-oleoyltaurate, oleic acid ester of sodium isethionate, dioctyl sodium sulfosuccinate sodium dodecyldiphenyloxide disulfonate.

Among nonionic compounds preferred members are alkyl phenoxy poly (ethyleneoxy) ethanols such as nonyl phenol adducts with ethylene oxide; trimethyl nonyl polyethylene glycol ethers, polyethylene oxide adducts of fatty and resin acids, and long-chain alkylmercaptan adducts with ethylene oxide.

In the compositions of the present invention the ratio of the benzoic acid compounds to the surfactants ranges from 1:16 to 30:1 by weight. Generally the ratios representing greater amounts of surfactant are preferred when applying compositions of the present invention in dilute solutions. When applied in more concentrated solutions the ratios by weight of the benzoic acid compound to the surfactant are preferably those representing smaller amounts of surf ctant.

A felativ'ely dilute solution is prepared, for example, w'lir'i fdur ts eight pounds of the benzoic acid compounds are added t6 100 gallons of water. Accordingly, the preferred ratio of the befiioiac'id compounds to surfactants ranges from about 1:16 to 2: 1

A relatively concentrated solution is prepared when about four to eight pounds of the benzoic acid compounds are added to seven to fifteen gallons of water. In such solutions the ranges of the ratio of the benzoic acid compounds to the surfactants can be from 1:1 to 30:1 with the more preferred ranges being 1:1 to 10:1.

It has been found that the application of proper amounts of the benzoic acid compounds, with or without surfactants, upon sugar cane at an appropriate time subsequent to planting and prior to harvest produces desirable hormonal affects upon the siigaf ease evidenced by an increased sugar yield. x

The amount of the benzoic acid compounds applied to sugar cane will range from A pound per acre to ten pounds per acre with a preferred range from 4 pound per acre to four pounds per acre. The smaller amounts ranging between A pound per acre and /4 pound per acre produce the advantageous effects of the present invention but generally are of lesser magnitude than the effects usual- 1y desired. The larger amounts ranging between four pounds per acre tl'ifotigh ten pounds per acre in some circumstances can be used but in general, there can be some measure of damage to the sugar cane tl the amount increases much above four pounds per acre.

Application of the benzoic acid compounds is made to sugar cane at a time prior to harvest and especially prior to the time the sugar cane has reached maximum sugar content. Theoretically, the composition of the present invention can be applied to sugar cane at any time subsequent to the first signs of sugar production therein and prior to the complete ripening thereof. Preferably the composition will be applied at about /2 to three months prior to harvest with application about one month prior to harvest being especially advantageous.

It is not understood precisely what happens in the metabolism of sugar cane when the benzoic acid compounds are added according to the invention but it appears probable that the plants metabolism is modified such that its efforts are directed more to the conversion of various structures present to the desired sugar. It is also probable that the application of the benzoic acid compound to growing sugar cane prevents the formation of new plant tissue such that the plants energies are more concentrated on the production of sugar.

In order that the invention may be better understood reference should be had to the following illustrative example.

A composition is prepared with:

Percent 2,3-dichloro-6-methylbenzoic acid,

triethanolamine salt 50 Trimethylnonyl polyethylene glycol ether 50 In the foregoing example instead of using the triethanolamine salt an equal amount of the acid chloride, or the sodium, potassium, ammonium, monomethylamine, diethylamine, triethylamine, ethanolamine and diethanolamine salts can be employed with substantially like results.

Also similar results differing only in magnitude of effect are obtained by using the above compositions at concentrations of one pound, two pounds, four pounds, six pounds and eight pounds in fifteen gallons of water instead of the foregoing three pounds per fifteen gallons of water.

I claim:

1. A method for increasing the maximum sugar content of sugar cane comprising the application to maturing sugar cane /2 to three months prior to the harvest thereof, of a solution containing a benzoic acid compound of the formula COOH and its salts, where X is selected from the group consisting of chlorine and methyl but at least one X is methyl, the application of said solution being at the rate equivalent to apply from .1 to 10 pounds of said benzoic acid compound per acre of sugar cane being treated.

2. A method for increasing the maximum sugar content of sugar cane comprising the application to maturing sugar cane one to three months prior to the harvest thereof, of a composition comprising a benzoic acid compound of the formula and its salts, where X is selected from the group consisting of chlorine and methyl but at least one X is methyl, in admixture with a surface-active agent, the ratio of said benzoic acid compound to said surface active agent ranging from 1:16 to 30:1 by weight and the application of said composition being at the rate equivalent to apply from .1 to 10 pounds of said benzoic acid compound per acre of sugar cane being treated.

3. A method for increasing the maximum sugar content of sugar cane comprising the application to maturing sugar cane one to three months prior to the harvest thereof, of a composition comprising a benzoic acid compound of the formula and its salts, where X is selected from the group consisting of chlorine and methyl but at least one X is methyl, in admixture with a surface-active agent selected from the group consisting of alkyl and alkyl aryl polyether alcohols, polyoxyethylene sorbital and sorbitan acid esters co-reacted with ureas, polyethylene glycol fatty esters and fatty alkylol amide condensates, alkyl aryl sulfonates, fatty alcohol sulfates, dialkyl esters of sodium sulfosuccinate, fatty acid esters of sodium isethionate, polyoxyethylene thioether, long-chain quaternary ammonium chloride, dodecylbenzene sulfonic acid, sodium lauryl sulfate, alkyl naphthalene sulfonates, sodium N-methyl-N-o1eoyltaurate, oleic acid esters of sodium isethionate, dioctyl sodium sulfosuccinate sodium dodecyldiphenyloxide disulfonate, nonyl phenol adducts with ethylene oxide; trimethyl nonyl polyethylene glycol ethers, polyethylene oxide adducts of fatty and resin acids, and long-chain alkylmercaptan adducts with ethylene oxide, the ratio of said benzoic acid compound to said surface active agent ranging from 1:16 to 30:1 by Weight and the application of said composition being at the rate equivalent to apply from .1 to 10 pounds of said benzoic acid compound per acre of sugar cane being treated.

References Cited by the Examiner UNITED STATES PATENTS 2,394,916 2/1946 Jones 7l2.6 3,008,818 11/1961 Guth 7l-2.6

FOREIGN PATENTS 1,224,787 2/ 1960 France.

OTHER REFERENCES Chemical Abstracts, vol. 53, col. 117390) (1959).

LEWIS GOTTS, Primary Examiner. 

1. A METHOD FOR INCREASING THE MAXIMUM SUGAR CONTENT OF SUGAR CANE COMPRISING THE APPLICATION TO MATURING SUGAR CANE 1/2 TO THREE MONTHS PRIOR TO THE HARVEST THEREOF, OF A SOLUTION CONTAINING A BENZOIC ACID COMPOUND OF THE FORMULA 